Formaldehyde → Octrizole

HRID 257660

Reaktionsgleichung

Reaktionsgleichung von HRID 257660
[OH-].[Na+].[N+:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]=[N:13][C:14]1[CH:19]=[C:18]([C:20]([CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:22])[CH3:21])[CH:17]=[CH:16][C:15]=1[OH:28])([O-])=O.C1C2C(=O)C3C(=CC=CC=3)C=2C=CC=1.C=O.S(=O)(=O)(O)O>O.CO>[OH:28][C:15]1[CH:16]=[CH:17][C:18]([C:20]([CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:22])[CH3:21])=[CH:19][C:14]=1[N:13]1[N:12]=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]2=[N:3]1

Komponenten

8

Edukt 5

HCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 10241FluorenoneHCID 14798Sodium HydroxideHCID 1039272-((2-Nitrophenyl)azo)-4-(1,1,3,3-tetramethylbutyl)phenol

Produkt 1

HCID 62485OctrizoleAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

Example 11 of U.S. Pat. No. 4,780,541 is duplicated. This is an example of the use of an aldehyde reducing agent and the aromatic ketone 9-fluorenone as a catalyst. Methanol (110 ml), water (20 ml), 97% sodium hydroxide (12.4 g), and 2-nitro-2'-hydroxy-5'-t-octylazobenzene (17.8 g) are mixed and stirred. After adding 9-fluorenone (2.4 g) to the resultant mixture at 65° to 70° C., 80% paraformaldehyde (6 g) is added to the mixture for 4 hours, and then the reaction liquor is further stirred at the boiling point (73° C. ) for 6 hours, thus the reduction reaction having completed. Thereafter, water (50 ml) is added to the reaction liquor, and the reaction liquor is neutralized to pH 8 with 62% sulfuric acid (16 g) to precipitate a crystal. The crystal thus obtained is filtered by suction to separate the crystal, and the separated crystal is fully washed with water and further with methanol. The washed crystal is then dried, thus producing 13.1 g of 2-(2-hydroxy-5-t-octylphenyl)benzotriazole having a melting point of 103° to 105° C. at the yield of 81.0%. One can see that the reaction takes over 10 hours to complete.

Aufarbeitung

  1. stirringthe reaction liquor is further stirred at the boiling point (73° C. ) for 6 hours
  2. customthus the reduction reaction
  3. customto precipitate a crystal
  4. customThe crystal thus obtained
  5. filtrationis filtered by suction
  6. customto separate the crystal
  7. washthe separated crystal is fully washed with water and further with methanol
  8. customThe washed crystal is then dried

Quellen und Nachweise

ORD-Eintrag
ord-ccab13c5456a476d987ab058d540093f
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05262541

Verknüpfte Notizen

Wird geladen…